Water-soluble substituted aminocarbonyl monoazo dyestuffs

ABSTRACT

Water-soluble monoazo dyestuffs are described, which, in the form of the free acid, correspond to the formula ##STR1## wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10  and A have the meaning indicated in the description, and their preparation and suitability for dyeing natural and synthetic fibre materials, in particular for dyeing polyamide fibres.

This is a continuation of application Ser. No. 51,660 filed June 25, 1979, now abandoned, which is a continuation of Ser. No. 940,669, filed Sept. 8, 1978, now abandoned.

The invention relates to water-soluble monoazo dyestuffs which, in the form of the free acid, correspond to the formula ##STR2## wherein R₁ and R₂ denote hydrogen, halogen, phenoxy, C₁ -C₄ -alkoxy, C₁ -C₄ -alkyl, thiocyano, trifluoromethyl, phenylsulphonyl, C₁ -C₁₂ -alkylsulphonyl as well as carbamoyl or sulphamoyl, it being possible for the carbamoyl and sulphamoyl groups to be monosubstituted or disubstituted by C₁ -C₁₂ -alkyl which is optionally substituted by C₁ -C₄ -alkoxy, cyclohexyl, chlorine, hydroxyl, cyano or phenyl, cyclohexyl, cyclopentyl or phenyl which is optionally substituted by C₁ -C₄ -alkyl, cyclohexyl, C₁ -C₄ -alkoxy, chlorine, bromine or cyano,

R₃ denotes hydrogen, chlorine or bromine,

R₄ denotes hydrogen, C₁ -C₄ -alkyl, halogen or C₁ -C₄ -alkoxy,

R₅ and R₆ denote hydrogen, optionally substituted alkyl or optionally substituted aralkyl,

R₇ denotes hydrogen or C₁ -C₄ -alkyl,

R₈, R₉ and R₁₀ denote hydrogen, C₁ -C₄ -alkyl, halogen, C₁ -C₄ -alkoxy or cyano and

A denotes a bridge member or a direct bond.

Suitable alkyl radicals R₅ and R₆ are, in particular, C₁ -C₄ -alkyl radicals which can be substituted by halogen, cyano, C₁ -C₄ -alkoxy, hydroxyl, C₁ -C₄ -alkoxycarbonyloxy, C₁ -C₄ -alkylcarbonyloxy, C₁ -C₄ -alkylcarbonylamino or phenylcarbonylamino.

Suitable aralkyl radicals R₅ and R₆ are, in particular, benzyl and 2-phenethyl, it being possible for the phenyl radical of these groups to be optionally further substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, halogen or cyano.

Examples of suitable bridge members A and C₁ -C₄ -alkylene, C₁ -C₄ -alkyleneoxy, oxy-C₁ -C₄ -alkylene, oxy-C₂ -C₄ -alkyleneoxy, C₁ -C₄ -alkylenecarbonyl, C₁ -C₄ -alkylenecarbonyloxy, C₁ -C₄ -alkyleneoxycarbonyl, C₁ -C₄ -alkyleneoxycarbonylamino, --O--, --NH-- and amino-C₁ -C₄ -alkylene.

Preferred dyestuffs are those which, in the form of the free acid, correspond to the formula ##STR3## wherein R₁, R₂ and R₃ have the abovementioned meaning,

R₄ ' denotes hydrogen, methyl, methoxy or ethoxy,

R₅ ' and R₆ ' denote C₁ -C₄ -alkyl, which can be further substituted by C₁ -C₄ -alkoxy, chlorine, cyano, hydroxyl, C₁ -C₄ -alkoxycarbonyloxy, C₁ -C₄ -alkylcarbonyloxy, C₁ -C₄ -alkylaminocarbonyloxy or phenylaminocarbonyloxy, or phenethyl or benzyl,

R₈ ' and R₉ ' denote hydrogen, chlorine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl or cyano and

A' denotes a direct bond, methylene, ethylene, methyleneoxy, ethyleneoxy, methyleneoxycarbonyl, ethyleneoxycarbonyl, propyleneoxycarbonyl, methyleneoxycarbonylamino, ethyleneoxycarbonylamino, oxyethyleneoxy, oxyisopropyleneoxy, oxyisobutyleneoxy, --O--, --NH--, aminomethylene or aminoethylene.

Particularly preferred dyestuffs are those which, in the form of the free acid, correspond to the formula ##STR4## wherein R₈ ' and R₉ ' have the abovementioned meaning,

A" denotes a direct bond, NH, CH₂ --O, CH₂ or C₂ H₄,

R₁ ' denotes hydrogen, chlorine, bromine or trifluoromethyl,

R₂ ' denotes hydrogen or chlorine,

R₅ " denotes methyl or ethyl,

R₆ " denotes methyl, ethyl or cyanoethyl, and

R₁₁ denotes benzyl, phenyl which is optionally substituted by chlorine or methyl, or a radical of the formula ##STR5## R₁₂ denotes hydrogen or C₁ -C₄ -alkyl and R₁₃ denotes C₁ -C₁₂ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, phenyl which is optionally substituted by methyl, ethyl, chlorine, methoxy or ethoxy, or benzyl, phenethyl, cyclohexyl or methylcyclohexyl.

Within the dyestuffs of the formula (III), the dyestuffs which, in the form of the free acid, correspond to the formula ##STR6## wherein A", R₁₂ and R₁₃ have the abovementioned meaning,

R₈ " denotes hydrogen, chlorine, methoxy, ethoxy or methyl and

R₉ " denotes hydrogen, chlorine or methyl are preferred.

The dyestuffs of the formula (I) are prepared by diazotising an amine of the formula ##STR7## wherein R₁, R₂ and R₃ have the abovementioned meaning, and coupling the diazotisation product to coupling components of the formula ##STR8## wherein R₄, R₅, R₆, R₇, R₈, R₉, R₁₀ and A have the meaning indicated above.

The dyestuffs according to the invention are suitable for dyeing natural and synthetic fibre materials, in particular for dyeing polyamide fibres in level, deep yellowish-tinged to bluish-tinged red shades of very good fastness to light. They are already absorbed well onto polyamide fibres in a neutral to weakly acid dyebath. By polyamide fibres there are understood here, in particular, those made of synthetic polyamides, such as ε-polycaprolactam or condensation products of adipic acid and hexamethylenediamine. The dyestuffs are used either in the form of the free acids or in the form of their salts, in particular the alkali metal salts, preferably the sodium salts or potassium salts, as well as the ammonium salts.

EXAMPLE 1

2.4 g of 4-(N-methyl-N-cyclohexylaminosulphonyl)-2,5-dichloroaniline are dissolved in 100 ml of glacial acetic acid. 30 ml of concentrated HCl are added and the amine is diazotised at 0° C. with 5 ml of a 10% strength NaNO₂ solution. 2.7 g of 3-(4-methoxy-3-sulphobenzoyl-amino)-N,N-diethylaniline are dissolved in 50 ml of 1 N NaOH. The alkaline solution of the coupling component is added to the diazonium salt solution at 0° C. and the pH is adjusted to about 4 with sodium acetate solution. The dyestuff of the formula ##STR9## which has precipitated is filtered off and dried at 40° C.

The coupling component of the formula ##STR10## was prepared by reacting p-methoxybenzoyl chloride with 3-N,N-diethylamino-aniline in toluene in the presence of NaHCO₃ and after-sulphonating the product at 60° C. in 100% strength sulphuric acid with 20% of oleum.

DYEING EXAMPLE 1

0.1 g of the dyestuff from Example 1 is dissolved hot in 100 ml of water, 5 ml of 10% strength ammonium acetate solution are added and the mixture is diluted to a volume of 500 ml of with water. 10 g of polyamide fibres are introduced into the dyebath, the dyebath is brought to the boil in the course of 20 minutes, 4 ml of 10% strength acetic acid are added and the bath is boiled for one hour. Thereafter, the fibres are rinsed and dried at 70° to 80° C. A dyeing in a bluish-tinged red shade with good fastness properties in use, in particular with very good fastness to wet processing, is obtained.

EXAMPLE 2

2.4 g of 4-(N-methyl-N-cyclohexylaminosulphonyl)-2,5-dichloroaniline are dissolved and diazotised analogously to Example 1. 3.3 g of 3-(4-sulpho-2-chloro-phenoxy-acetylamino)-N,N-diethylaniline are dissolved in 60 ml of half-concentrated acetic acid and the solution is added to the diazonium salt solution. The pH is adjusted to about 4 with sodium acetate solution.

The dyestuff of the formula ##STR11## which has precipitated is filtered off and dried at 40° C. The dyestuff dyes polyamide fabric in a bluish-tinged red shade with good fastness properties in use, in particular with very good fastness to wet processing.

The acid coupling component was prepared from the compound of the formula ##STR12## which has been prepared by customary processes, by after-sulphonation at 100° C. in sulphuric acid monohydrate.

If the procedure is as in Example 1 and 2, using the corresponding diazo and coupling components, further dyestuffs of the general formula VII which follows having the substituent meanings and colour shades indicated in the table which follows are obtained. The dyestuffs are water-soluble, dye polyamide in orange to ruby-red shades from a weakly acid or neutral bath and, in particular, are very fast to wet processing. The dyestuffs are furthermore distinguished by the fact that they are not sensitive to hard water. ##STR13##

"x-sulpho" in the table means that the precise position of the sulpho group in ring B is unknown.

                                      TABLE 1                                      __________________________________________________________________________     Example                                                                             R.sub.12       R.sub.13                                                                           A       Substituents on B                                                                            Colour shade                     __________________________________________________________________________      3   phenyl         methyl                                                                             --CH.sub.2 --O--                                                                       2-chloro-4-sulpho                                                                            bluish-tinged red                 4   benzyl         H   "       "             "                                 5   phenethyl      H   "       "             "                                 6   o-tolyl        H   "       "             "                                 7   p-ethylphenyl  H   "       "             "                                 8   3-chloro-4-methylphenyl                                                                       H   "       "             "                                 9   2-methoxyphenyl                                                                               H   "       "             "                                10   2-methoxy-5-chlorophenyl                                                                      H   "       "             "                                11   2-methylcyclohexyl                                                                            H   "       "             "                                12   butyl          butyl                                                                              "       "             "                                13   butyl          butyl                                                                              "       4-sulpho      "                                14   butyl          butyl                                                                              "       2-methyl-4-chloro-6-sulpho                                                                   "                                15   butyl          butyl                                                                              "       2,4-dichloro-6-sulpho                                                                        "                                16   butyl          butyl                                                                              "       2-methyl-4-sulpho-5-sulpho                                                                   "                                17   cyclohexyl     methyl                                                                             "       2-methyl-4-chloro-6-sulpho                                                                   "                                18   2-methylcyclohexyl                                                                            methyl                                                                             "       3-sulpho-4-methoxy                                                                           "                                19   phenyl         methyl                                                                             "       "             "                                20   4-biphenylyl   methyl                                                                             "       "             "                                21   butyl          butyl                                                                              "       "             "                                22   ethyl          ethyl                                                                              "       "             "                                23   butyl          H   "       "             "                                24   butoxybutyl    H   "       "             "                                25   butoxybutyl    H   "       3-methoxy-x-sulpho                                                                           "                                26   methyl         methyl                                                                             "       "             "                                27   phenethyl      H   "       3-sulpho-4-methoxy                                                                           "                                28   benzyl         benzyl                                                                             "       "             "                                29   cyclohexylmethyl                                                                              H   --NH--  4-sulpho      "                                30   cyclohexyl     methyl                                                                             "       "             "                                31   butyl          butyl                                                                              "       "             "                                32   phenyl         ethyl                                                                              "       "             "                                33   phenyl         methyl                                                                             "       "             "                                34   phenethyl      H   "       "             "                                35   4-ethylphenyl  H   "       "             "                                36   2,5-dimethylphenyl                                                                            H   "       "             "                                37   2-ethoxyphenyl H   "       "             "                                38   cyclohexyl     methyl                                                                             "       2-sulpho-4-methyl                                                                            "                                39   hexyl          H   "       2-sulpho-4-chloro                                                                            "                                40   octyl          methyl                                                                             "       x-sulpho-4-ethoxy                                                                            "                                41   4-cyclohexyl-2-methylphenyl                                                                   H   "       2-sulpho-4-methyl                                                                            "                                42   phenyl         H   --      2-sulpho      yellowish-tinged                                                               red                              43   phenylethyl    H   CH.sub.2                                                                               x-sulpho-4-methyl                                                                            red                              44   benzyl         methyl                                                                             "       "             "                                45   cyclohexyl     H   "       "             "                                46   2-methylphenyl H   CH.sub.2 --CH.sub.2                                                                    x-sulpho      "                                47   4-chlorobenzyl H   "       "             "                                48   phenylethyl    methyl                                                                             "       x-sulpho-4-methyl                                                                            bluish-tinged red                49   2,5-diethoxyphenyl                                                                            H   "       2-chloro-5-methyl-x-sulpho                                                                   "                                50   cyclohexylethyl                                                                               H   "       "             yellowish-tinged                                                               red                              51   2-methyl-4-cyclohexylphenyl                                                                   H   "       "             yellowish-tinged                                                               red                              52   octyl          methyl                                                                             --NH--  2,5-dichloro-4-sulpho                                                                        bluish-tinged red                53   benzyl         ethyl                                                                              "       2-chloro-4-sulpho-5-methyl                                                                   "                                54   phenylethyl    H   O       x-sulpho      red                              55   phenylethyl    H   --CH.sub.2 O--                                                                         2-methyl-3,5-dichloro-4-                                                                     bluish-tinged red                                                sulpho                                         56   phenylethyl    H   OC.sub.2 H.sub.4 O                                                                     4-sulpho      "                                57   2-cyanoethyl   H   NH--CH.sub.2                                                                           x-sulpho      "                                58   2-methoxyethyl H   N--C.sub.2 H.sub.4                                                                     "             "                                59   2-methoxyethyl H   C.sub.2 H.sub.4 OCONH                                                                  "             red                              60   propyl         H   C.sub.2 H.sub.4 OCO                                                                    2-sulpho      "                                61   butyl          methyl                                                                             "       "             "                                __________________________________________________________________________

Further dyestuffs for polyamide are prepared by diazotisation and coupling in the customary manner, using the diazo components and coupling components given in Table 2, which follows.

                                      TABLE 2                                      __________________________________________________________________________     Example                                                                               Diazo component       Coupling component                                                                               Colour shade                    __________________________________________________________________________     62   2-trifluoromethyl-4-hexylamino-                                                                      N,N-diethyl-3-(2-sulpho-4-chloro-                                                                bluish-tinged red                      sulphonyl-5-chloroaniline                                                                            phenyl)-aminocarbonylaminoaniline                   63   2-trifluoromethyl-4-hexylamino-                                                                      N,N-diethyl-3-(3-chloro-4-sulpho-                                                                yellowish-tinged red                   sulphonylaniline      phenyl)-aminocarbonylaminoaniline                                                                "                                      2-trifluoromethyl-4-hexylamino-                                                                      N,N-diethyl-3-(x-sulpho-4-ethoxy-                        sulphonylaniline      phenyl)-aminocarbonylaminoaniline                   65   2,5-dichloro-4-phenyl-                                                                               N,N-diethyl-3-(x-sulpho-4-ethoxy-                                                                bluish-tinged red                      sulphonylaniline      phenyl)-aminocarbonylaminoaniline                   66   2,5-dichloro-4-(4-methyl-                                                                            N,N-diethyl-3-(x-sulpho-4-ethoxy-                                                                "                                      phenyl)-sulphonylaniline                                                                             phenyl)-aminocarbonylaminoaniline                   67   2-phenylsulphonyl-4-bromo-                                                                           N,N-diethyl-3-(x-sulpho-4-ethoxy-                                                                red                                    aniline               phenyl)-aminocarbonylaminoaniline                   68   2-phenylsulphonyl-5-  N,N-diethyl-3-(x-sulpho-4-ethoxy-                                                                yellowish-tinged red                   trifluoromethylaniline                                                                               phenyl)-aminocarbonylaminoaniline                   69   2-phenylsulphonyl-5-phenyl-                                                                          N,N-diethyl-3-(x-sulpho-4-ethoxy-                                                                "                                      aminocarbonylaniline  phenyl)-aminocarbonylaminoaniline                   70   2-phenylsulphonyl-5-dimethyl-                                                                        N,N-diethyl-3-(x-sulpho-4-ethoxy-                                                                "                                      aminosulphonylaniline phenyl)-aminocarbonylaminoaniline                   71   2-phenylsulphonylaniline                                                                             N,N-diethyl-3-(2-sulpho-4-                                                                       reddish-tinged orange                                        methylphenyl)-aminocarbonyl-                                                   aminoaniline                                        72   "                     N,N-diethyl-3-(2-chloro-4-methyl-                                                                "                                                            6-sulphophenyl)-aminocarbonyl-                                                 aminoaniline                                        73   "                     N,N-diethyl-3-(4-sulphophenoxy)-                                                                 "                                                            methylcarbonylaminoaniline                          74   "                     N,N-diethyl-3-(2-chloro-4-sulpho-                                                                "                                                            phenoxy)-methylcarbonylaminoaniline                 75   2-phenylsulphonyl-4-bromo-5-                                                                         N,N-diethyl-3-(2-chloro-4-sulpho-                                                                bluish-tinged red                      methylsulphonylaniline                                                                               phenoxy)-methylcarbonylaminoaniline                 76   2,5-bis-phenylsulphonyl-4-                                                                           N,N-diethyl-3-(2-methoxy-5-                                                                      "                                      bromoaniline          sulphophenyl)-carbonylaminoaniline                  77   2,5-bis-phenylsulphonyl-4-                                                                           N,N-diethyl-3-(3-sulpho-4-ethoxy-                                                                "                                      bromoaniline          phenyl)-carbonylaminoaniline                        78   2,5-dichloro-4-benzyl-                                                                               N,N-diethyl-3-(2-sulphophenyl)-                                                                  yellowish-tinged red                   sulphonylaniline      carbonylaminoaniline                                79   2-phenylsulphonyl-5-benzyl-                                                                          N,N-diethyl-3-(2-sulphophenyl)-                                                                  scarlet                                aminosulphonylaniline carbonylaminoaniline                                80   2-(4-methylphenyl)-sulphonyl-                                                                        N,N-diethyl-3-(2-sulphophenyl)-                                                                  yellowish-tinged red                   4-chloro-5-benzylamino-                                                                              carbonylaminoaniline                                     sulphenylaniline                                                          81   2-phenylsulphonyl-4-bromo-                                                                           N,N-diethyl-3-(x-sulpho-4-methyl-                                                                "                                      aniline               benzyl)-carbonylaminoaniline                        82   2-ethylsulphonyl-5-trifluoro-                                                                        N,N-diethyl-3-sulphophenylethyl-                                                                 "                                      methylaniline         carbonylaminoaniline                                83   2-phenylsulphonyl-4-bromo-5-                                                                         N,N-diethyl-3-sulphophenylethyl-                                                                 bluish-tinged red                      phenylaminocarbonylaniline                                                                           carbonylaminoaniline                                84   2-trifluoromethyl-4-(N-phenyl-                                                                       N,N-diethyl-3-(x-sulpho-4-methyl-                                                                scarlet                                ethyl-N-methylsulphonyl)-                                                                            phenylethyl)-carbonylaminoaniline                        aniline                                                                   85   3-phenylsulphonyl-4-ethylamino-                                                                      N,N-diethyl-3-(x-sulpho-4-methyl-                                                                "                                      carbonylaniline       phenylethyl)-carbonylaminoaniline                   86   3-methylaminosulphonyl-4-phenyl-                                                                     N,N-diethyl-3-(x-sulpho-4-methyl-                                                                "                                      sulphonylaniline      phenylethyl)-carbonylaminoaniline                   87   2,5-diethoxy-4-phenylamino-                                                                          N,N-diethyl-3-(x-sulpho-2-chloro-                                                                bluish-tinged red                      sulphonylaniline      4-methoxyphenyl)-aminocarbonyl-                                                amino                                               88   2-bromo-4-phenylaminocarbonyl-                                                                       N,N-diethyl-3-(x-sulpho-2-chloro-                                                                scarlet                                aniline               4-methoxyphenyl)-aminocarbonyl-                                                amino                                               89   2-bromo-4-phenylaminocarbonyl-                                                                       N,N-diethyl-3-(4-sulphophenoxy)-                                                                 "                                      aniline               methylcarbonylaminoaniline                          90   2-methyl-4-phenylamino-                                                                              N,N-diethyl-3-(4-sulphophenoxy)-                                                                 yellowish-tinged scarlet               carbonylaniline       methylcarbonylaminoaniline                          91   2-methyl-4-phenylamino-                                                                              N-2-cyanoethyl-N-ethyl-3-(2-                                                                     "                                      carbonylaniline       methyl-4-sulphophenoxy)-methyl-                                                carbonylaminoaniline                                92   2-bromo-4-dimethylamino-                                                                             N-benzyl-N-ethyl-3-(4-sulpho-                                                                    yellowish-tinged red                   sulphonylaniline      phenoxy)-ethylcarbonylamino-                                                   aniline                                             93   2-phenylsulphonyl-5-methyl-                                                                          N-(2-acetoxyethyl)-N-ethyl-3-                                                                    "                                      sulphonylaniline      sulphophenylaminocarbonyloxy-                                                  methylcarbonylaminoaniline                          94   2,5-dichloro-4-methylamino-                                                                          N-(2-acetoxyethyl)-N-ethyl-3-                                                                    red                                    sulphonylaniline      sulphophenylaminocarbonyloxy-                                                  methylcarbonylaminoaniline                          95   2,4-dibromo-6-phenylsulphonyl-                                                                       N-(2-methoxycarbonyloxyethyl)-                                                                   "                                      amiline               N-ethyl-3-(2-sulphophenyl)-                                                    carbonyloxymethylcarbonyl-                                                     aminoaniline                                        96   2,4-bis-phenylsulphonylaniline                                                                       N,N-diethyl-3-(x-sulphophenoxy)-                                                                 "                                                            carbonylaminoaniline                                97   2-trifluoromethyl-4-phenyl-                                                                          N,N-diethyl-3-(x-sulphophenoxy)-                                                                 scarlet                                sulphonylaniline      carbonylaminoaniline                                98   2,5-dichloro-4-phenylethyl-                                                                          N,N-diethyl-3-(4-sulphophenoxy-                                                                  bluish-tinged red                      aminosulphonylaniline sec.-butoxycarbonylaminoaniline                     99   2-trifluoromethyl-4-(4-butoxy-                                                                       N,N-diethyl-3-(x-sulphobenzyl)-                                                                  yellowish-tinged red                   butyl)-aminosulphonylaniline                                                                         aminocarbonylaminoaniline                           100  2,5-dichloro-4-tert.-butyl-                                                                          N,N-bis-(2-acetoxyethyl)-3-(2-                                                                   scarlet                                aminosulphonylaniline sulphophenyl)-carbonylaminoaniline                  101  2,6-dichloro-4-benzylamino-                                                                          N,N-diethyl-3-(x-sulpho-4-methyl-                                                                red                                    sulphonylaniline      benzyl)-carbonylaminoaniline                        102  2-phenylaminocarbonyl-4-phenyl-                                                                      N,N-diethyl-3-(2-chloro-x-sulpho-                                                                "                                      aminosulphonylaniline 5-methylphenyl)-ethylcarbonyl-                                                 aminoaniline                                        103  2,5-dichloro-4-tert.-butyl-                                                                          N-[2-(2,4-dichloro-6-methyl-                                                                     bluish-tinged red                      aminosulphonylaniline phenyl)-aminocarbonylaminoethyl]-                                              N-ethyl-3-(4-sulphophenyl)-amino-                                              carbonylaminoaniline                                104  2,5-dichloro-4-tert.-butyl-                                                                          N-(2-ethylaminocarbonyloxyethyl)-                                                                "                                      aminosulphonylaniline N-ethyl-3-(4-sulphophenoxy)-methyl-                                            carbonylaminoaniline                                105  3,5-bis-trifluoromethylaniline                                                                       N-(2-cyanoethyl)-N-phenylethyl-                                                                  orange                                                       3-(4-sulphophenyl)-aminocarbonyl-                                              aminoaniline                                        106  2-chloro-4-thiocyanoaniline                                                                          N,N-bis-(2-butoxyethyl)-3-(x-                                                                    "                                                            sulphophenoxy)-sec.-butyl-                                                     carbonylaminoaniline                                107  2,5-dichloro-4-(2-hydroxy-                                                                           N-ethyl-N-(2-chloroethyl)-3-(2-                                                                  bluish-tinged red                      ethyl)-aminosulphonylaniline                                                                         chloro-4-sulpho-5-ethoxyphenyl)-                                               carbonylaminoaniline                                108  2,5-dichloro-4-(4-cyanobutyl)-                                                                       N-(2-chloroethyl)-N-ethyl-3-(2,5-                                                                "                                      aminosulphonylaniline dimethyl-3-ethoxy-x-sulphophenyl)-                                             carbonylaminoaniline                                109  2-trifluoromethyl-4-dimethyl-                                                                        N,N-diethyl-3-(x-sulpho-3-methoxy-                                                               yellowish-tinged red                   aminosulphonylaniline phenyl)-carbonylaminoaniline                        110  2-trifluoromethyl-4-phenyl-                                                                          N,N-diethyl-3-(3-sulpho-4-methoxy-                                                               "                                      ethylaminosulphonylaniline                                                                           phenyl)-carbonylaminoaniline                        111  2-trifluoromethyl-4-(3-chloro-                                                                       N,N-diethyl-3-(3-sulpho-4-methoxy-                                                               "                                      4-methylphenyl)-aminosulphonyl-                                                                      phenyl)-carbonylaminoaniline                             aniline                                                                   112  2-trifluoromethyl-4-diethyl-                                                                         N,N-diethyl-3-(3-sulpho-4-methoxy-                                                               bluish-tinged red                      aminosulphonyl-5-chloroaniline                                                                       phenyl)-carbonylaminoaniline                        113  2-trifluoromethyl-4-diethyl-                                                                         N,N-diethyl-3-(4-sulphophenoxy)-                                                                 "                                      aminosulphonyl-5-chloroaniline                                                                       methylcarbonylaminoaniline                          114  2,5-dichloro-4-benzyl-                                                                               N,N-diethyl-3-(2-sulpho-4-methyl-                                                                "                                      sulphonylaniline      phenyl)-aminocarbonylaminoaniline                   115  2,5-dichloro-4-benzyl-                                                                               N,N-diethyl-3-(3-sulphophenyl)-                                                                  "                                      sulphonylaniline      aminocarbonylaminoaniline                           116  2,5-dichloro-4-diethylamino-                                                                         N,N-diethyl-3-(3-sulphophenyl)-                                                                  "                                      sulphonylaniline      aminocarbonylaminoaniline                           117  2,5-dichloro-4-diethylamino                                                                          N,N-diethyl-3-(4-sulphophenyl)-                                                                  "                                      sulphonylaniline      aminocarbonylaminoaniline                           118  2,5-dichloro-4-butoxypropyl-                                                                         N,N-diethyl-3-(4-methyl-x-sulpho-                                                                yellowish-tinged red                   aminosulphonylaniline benzyl)-carbonylaminoaniline                        119  4-cyclohexylmethylamino-                                                                             N,N-diethyl-3-(4-methyl-x-sulpho-                                                                "                                      sulphonyl-2,5-dichloro-aniline                                            120  2,5-dichloro-4-hexylamino-                                                                           N,N-diethyl-3-(4-methyl-x-sulpho-                                                                "                                      sulphonylaniline      benzyl)-carbonylaminoaniline                        121  2,5-dichloro-4-butoxypropyl-                                                                         N,N-diethyl-3-(x-sulphobenzyl)-                                                                  "                                      amino-sulphonylaniline                                                                               carbonylamino-aniline                               122  2,5-dichloro-4-N-methyl-N-                                                                           N,N-diethyl-3-(x-sulphobenzyl)-                                                                  "                                      cyclohexylaminosulphonyl-                                                                            carbonylamino-aniline                                    aniline                                                                   123  2,5-dichloro-4-phenethylamino-                                                                       N,N-diethyl-3-(x-sulphobenzyl)-                                                                  "                                      sulphonylaniline      carbonylamino-aniline                               124  4-cyclohexylaminosulphonyl-                                                                          N,N-diethyl-3-(x-sulphobenzyl)-                                                                  "                                      2,5-dicarbonaniline   carbonylamino-aniline                               __________________________________________________________________________ 

We claim:
 1. Water-soluble monoazo dyestuff which in the form of the free acid corresponds to the formula ##STR14## wherein R₈ ' and R₉ ' denote hydrogen, chlorine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl or cyano;A" denotes a direct bond, NH, CH₂ --O, CH₂ or C₂ H₄, R₁ ' denotes hydrogen, chlorine, bromine or trifluoromethyl, R₂ ' denotes hydrogen or chlorine, R₅ " denotes methyl or ethyl, R₆ " denotes methyl, ethyl or cyanoethyl, and R₁₁ denotes benzyl, phenyl which is optionally substituted by chlorine or methyl, or a radical of the formula ##STR15## R₁₂ denotes hydrogen or C₁ -C₄ -alkyl and R₁₃ denotes C₁ -C₁₂ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, phenyl which is optionally substituted by methyl, ethyl, chlorine, methoxy or ethoxy, or benzyl, phenethyl, cyclohexyl or methylcyclohexyl.
 2. Water-soluble monoazo dyestuffs according to claim 1, which, in the form of the free acid, correspond to the formula ##STR16## wherein A", R₁₂ and R₁₃ have the meaning given in claim 1,R₈ " denotes hydrogen, chlorine, methoxy, ethoxy or methyl and R₉ " denotes hydrogen, chlorine or methyl. 